15N and 195Pt N.M.R. Study of the Effect of Chain Length, n, on the Reactions of Amino Acids, + NH3(CH2)nCO2 -(n = 1, 2, 3), with Platinum(II) Ammine Complexes

Appleton T.G., Hall J.R. and Ralph S.F. (1985) 15N and 195Pt N.M.R. Study of the Effect of Chain Length, n, on the Reactions of Amino Acids, + NH3(CH2)nCO2 -(n = 1, 2, 3), with Platinum(II) Ammine Complexes. Australian Journal of Chemistry, 39 9: 1347-62. doi:10.1071/CH9861347


Author Appleton T.G.
Hall J.R.
Ralph S.F.
Title 15N and 195Pt N.M.R. Study of the Effect of Chain Length, n, on the Reactions of Amino Acids, + NH3(CH2)nCO2 -(n = 1, 2, 3), with Platinum(II) Ammine Complexes
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 1445-0038
Publication date 1985-01-01
Sub-type Article (original research)
DOI 10.1071/CH9861347
Volume 39
Issue 9
Start page 1347
End page 62
Total pages -1284
Subject 1600 Chemistry
Abstract 15N and 195Pt n.m.r. have been used to study the reactions in solution of cis-Pt(15NH3)2(H20)22+ (1), cis-Pt(15NH3)2(OH)2 (2), cis-Pt(15NH3)2Cl2 (3), Pt(15NH3)3(H2O)2+ (4) and Pt(15NH3)3(OH)+ (5), with the amino acids +NH3(CH2)nCO2 - (LH) [n = 1 (glycine, glyH); n = 2 (β-alanine, βalaH), n = 3 (γ-aminobutyric acid, abaH)]. While glycine with (1) gives initially cis-Pt(NH3)2(glyH-O)(H2O)2+, with facile ring closure to Pt(NH3)2(gly- N, O) +, ß-alanine and γ-aminobutyric acid with (1) give solutions containing a mixture of cis- Pt(NH3)2(LH-O)(H2O)2+, cis-Pt(NH3)2(LH-O)2 2+, and (Pt(NH3)2)2(µO,O.-LH)(µ-OH)3+, which are quite stable kinetically under mildly acid conditions. Ring closure to Pt(NH3)2(L- N, O)+ becomes increasingly difficult as n increases. At 37°C and initial pH 7, (3) with glycine gives Pt(NH3)2(gly-N, O)+, but ß-alanine and γ-aminobutyric acid give predominantly cis-Pt(NH3)2Cl(LH-O)+. Compound (4) with glycine gives initially Pt(NH3)3(glyH-O)2+, which then isomerizes to Pt(NH3)3(glyH-N)2+. In corresponding reactions with /3-alanine and y-aminobutyric acid, Pt(NH3)3(LH-O)2+ is stable indefinitely under mildly acid conditions. Differences in reactivity of the amino acids with (2) and (5) in alkaline solutions may be correlated with decreasing nucleophilicity of the amine group of NH2(CH2)nCO2 -as n increases.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
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